Cl2 / CCl4 reaction please help

[kov82]

so if you have 1-methylcyclopentene with Cl2/CCl4 ----> ant addition of Cl on both carbons + enantiomer, but does the Cl- ever attack carbon 2? attack on either carbon 1 or 2 would give you a vicinal dihalide in anti orientation

I ask because if 1-methylcyclopentene is mixed with Br2/aq NaCl, (ignoring the water reaction) you end up with Cl- on carbon 1 (the more highly substituted carbon, Markovnikov orientation) this was the answer in the book, but it never said that the Cl- in this case COULD NOT attack carbon 2 putting Br (from the halonium ion) on carbon 1 with the methyl group, you see what I'm asking? I know that -OH from the water reaction will give markovnikov orientation because the bond in the halonium ion is weaker for the more highly substituted carbon making that carbon easily attacked, but is it the same rules for the Cl-? I would think so but it made me wonder about the Cl2/CCl4 reaction if the Cl- ever attacks carbon 2 (the one without the methyl group) ?

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[hunterpostbacst]

I think you mixed up with other stuff.
1-methyl-pentene with Cl2/CCl4 ends up with anti-addition(2 Cl on the ring). The intermediate is a cyclic Cl intermediate and the another Cl do ATTACK the Carbon 2 because the metyl on C1 is hindered.

But, what you mixed up with other stuff is epoxides. When you have an epoxide, the nuclephile ATTACK the most least substituted carbon, called base-catalyzed addtion. Rather, the nucleophile attack the most substitued carbon when it is acid-catalyzed addtion.

So, when back to the point, Yes, the Cl attacks the C2.